Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.
A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3x OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.
Vieira
Adriano S
AS
Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, Brazil.
Fiorante
Pedro F
PF
Hough
Thomas L S
TL
Ferreira
Fernando P
FP
Lüdtke
Diogo S
DS
Stefani
Hélio A
HA
D001880:Boranes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002125:Calcium Gluconate / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D001880:Boranes; D001881:Borates; D006027:Glycosides; C021274:boron trifluoride; C098759:fluoroboric acid; D011188:Potassium; D002125:Calcium Gluconate